General and regioselective synthesis of substituted pyrroles by metal-catalyzed or spontaneous cycloisomerization of (Z)-(2-En-4-ynyl)amines

被引:119
作者
Gabriele, B [1 ]
Salerno, G
Fazio, A
机构
[1] Univ Calabria, Dipartimento Sci Farmaceut, I-87036 Cosenza, Italy
[2] Univ Calabria, Dipartimento Chim, I-87036 Cosenza, Italy
关键词
D O I
10.1021/jo034850j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl)amines I is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group, enynamines were stable and could be converted into the corresponding pyrroles by metal catalysis. CuCl2 was found to be an excellent catalyst for cycloisomerization of substrates substituted at C-3, while PdX2 in conjunction with KX (X = Cl, I) turned out to be a superior catalyst for the reaction of enynamines unsubstituted at C-3.
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页码:7853 / 7861
页数:9
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